Secret Confessions of a Smart Girl

It was the middle of the work day for him, but I work at home and make my own schedule. Lately I’ve noticed that I tend to spend more time online during regular business hours so that we can chat, and so that I can spend time shmooping with my girlfriend in another window. It’s not the most productive part of my day, but it’s a nice connection when the people you care about live several hours away.

I had just stated my intention to walk away from the computer to engage in some “focused daydreaming” to improve my mood. I was feeling tired, cranky, and a bit out of sorts, and I wasn’t certain if it was a euphemism for napping, masturbating, or cleaning out my closet. Fortunately he had his own ideas.

The phrase, “I think it would be appropriate for you to” is not usually followed by “find something just a bit larger than is entirely comfortable inside you, fuck yourself with it, and come for me.”

That time it was. Apparently, we are redefining the term “appropriate.” Not that I could find it in me to object. To blush behind my screen, yes. To be slightly horrified that he was telling me to do that from work, yes. To become instantly, enormously turned on - to deny it would be to lie.

So I went browsing through the sex toy drawer. I had actually done a big clean out around 6 months ago, and gotten rid of most of the toys that I considered to be too large for comfort, but I thought I still had one or two of them left. My favorite of the two I found - the vibrator I use when I want the sensation of being filled to be just on the right side of pain, when I want to fantasize that it’s “too big, too much” - wasn’t suitable for fucking, but it turned out that I had a toy of a similar width that was. A little short, perhaps, but wide enough that it would be difficult to push in, and shaped so that I could fuck myself with it and stay on the boundary of discomfort without falling over the edge.

My instructions were to fuck myself and come, that was all, and so I decided to take them literally. I would be allowed no other stimulation - no pain, no vibrator on my clit - my orgasm had to be from the sensations of the toy alone. It was my only allowable source for pleasure or pain.

I took off my clothes, put a condom on the toy, and heard his voice in my head as I slowly worked it into my cunt. As I thought, it was a little too wide for easy insertion. I had to push it in slowly, and firmly, and it still was a bit large to slide easily along my inner walls. I wanted to touch myself further, but I forced myself to follow the instructions I had been given and just slowly fuck myself with the toy - pushing it in far enough to hurt, and then twisting the head so that it would press against different places inside of me. I imagined that it was him fucking me, because in a way it was, and pictured him above me as I pushed the toy deep against my cervix so that it would make me ache while it finally made me come.

Then I came back to the computer to tell him what I’d done. It seemed, somehow, like it would be appropriate.